Organic compounds containing the trifluoromethyl group, perfluoroalkyl or polyfluoroalkyl groups find use as crop protection agents, pharmaceuticals and functional materials. In drugs, for example, the trifluoromethyl group is introduced mainly to increase metabolic stability and lipophilicity, to modulate the pKa of neighboring ionizable functional groups, and to impart weak C—F⋅⋅⋅X interaction. Compounds with perfluoroalkyl or polyfluoroalkyl groups connected to the nitrogen atom are rare and the methods of their preparation have hardly been explored. These compounds have a high potential to display unique physico-chemical and biological properties.
Organic azides are valuable intermediates in synthetic chemistry. Their ability to react with nucleophiles or electrophiles, to access nitrene chemistry by N2 elimination, or to act as dipoles in cycloadditions, underscores their versatility. The so called click reaction—Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC)—is a robust, effective and selective process widely used in organic synthesis, medicinal chemistry, in the chemistry of polymers and in chemical biology. Azidotrifluoromethane (CF3N3) is a known compound, which is thermally stable up to 300° C. and it was previously prepared in two steps from trifluoronitrosomethane (CF3NO) [K. O. Christe, C. J. Schack, Inorg. Chem. 1981, 20, 2566-2570]. The need to use not easily accessible starting materials, toxic and corrosive reagents and difficult synthesis precludes the use and investigation of properties of CF3N3. Longer carbon chain azidoperfluoroalkanes are not known, some azidopolyfluoroalkanes have been synthesized through the reaction of sodium azide with polyfluoroalkenes [C. G. Krespan, B. E. Smart, J. Org. Chem. 1986, 51, 320-326] or with halodifluoromethyl compounds [T. G. Archibald, K. Baum, J. Org. Chem. 1990, 55, 3562-3565]. In order to accelerate the development of applications and commercialization of CF3N3, azidoperfluoroalkanes and azidopolyfluoroalkanes, a more straightforward synthetic method is needed.